Playboy Retro: Hef's Personal Favorites

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.

Hugh Hefner is a connoisseur of uniquely beautiful women. It’s his singular talent for identifying and promoting ravishing and radiant girls that helped build the Playboy empire and has brought great joy to lovers of the female form for 60 years now. Obviously, Hef loves all the Playmates, but, over the years, a select few of these amazing women got a little closer to his heart. In this Playboy Retro we’re looking at some of the Playmates Hef dated and kept a little closer as his personal favorites.

Dark beauty Joni Mattis had a reputation as a shy girl, and her teasing pictorial for the November 1960 issue of Playboy is particularly coy (though in our opinion that’s part of the attraction of her shoot), but she had enough spunk to go toe-to-toe with one of the most gregarious men of all time, Mr. Hugh Hefner. She met him working on the set of the first Playboy TV series, Playboy’s Penthouse, and they soon started dating. Though they weren’t romantically involved for long, they remained lifelong friends and Joni later went on to work as the social secretary at the Playboy Mansion. You’re about to fall in love with her yourself!

Donna Michelle was 17 when she posed for Playboy as Miss December 1963, but by that time she was already an accomplished actress and ballerina. Her talent and bombshell looks (and 38D-22-37 figure) had a dynamite effect on Hef. They dated for a few whirlwind months and Donna later went on to appear in Playboy again as 1964’s Playmate of the Year. She also acted in a number of films like Beach Blanket Bingo, Agent for H.A.R.M. and The Spy with My Face.

We’ll take any reason to feature actress and musician Barbi Benton, the captivating cutie whose adorable sex appeal not only captured the imagination of a whole generation of men but also Hugh Hefner’s heart. The two met on the set of Playboy After Dark in 1969, when she was hired to cohost with Hef. After shooting two episodes, Hef asked Barbi out on a date, to which she said, “I don’t know, I’ve never dated anyone over 24 before.“ Hef replied, “That’s all right, neither have I.” This exchange began a relationship which lasted until 1976. Barbi was never a Playmate but she was on the cover of Playboy four times and starred in a number of pictorials. Now’s your chance to fall in love with her all over again.

We’ve trusted Hugh Hefner’s taste in women for 60 years now. Check out the gallery above of a few women he found especially delicious.